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Even at seven years old, Issa Rae meant business, conducting herself with entrepreneurial authority on a toy phone in her bedroom. Eventually, it was a matter of convincing others that she had a lot to say and getting them to listen. From her first web series, Awkward Black Girl, to network disappointments to HBO triumphs, Issa charts her aspirational journey—self-doubts and all—of being taken seriously, finding her voice, and shaping it into a groundbreaking career.

Remember a mortifying moment that made you self-aware? Honestly, Issa Rae remembers a few. In this illuminating essay, Issa follows her shoulda/coulda/woulda journey from awkward schoolgirl to a Hollywood life under the spotlight. Along the way she offers unfiltered insights into unwittingly courting controversy, curating a cautious but always authentic identity, and navigating the gap between private truth and public perception.